This invention relates to aminomethyl cyclododecanes selected from the group consisting of aminomethyl cyclododecane, bis-(aminomethyl)-cyclododecanes, tris-(aminomethyl)-cyclododecanes and mixtures thereof.
The present invention also relates to a process for producing these new compounds which is characterized in that cyclododeca-1,5,9-triene is reacted with carbon monoxide and hydrogen in the presence of a rhodium-containing catalyst at temperatures of from 80.degree. to 180.degree. C. and under pressures of from 30 to 900 bars. The catalyst is separated from the hydroformylation product and the hydroformylation products are treated with hydrogen in the presence of ammonia and a hydrogenation catalyst at from 50.degree. to 150.degree. C., optionally after separation by distillation into the individual components.
The present invention also relates to the use of the new compounds as corrosion inhibitors in heating oils, lubricants or motor fuels based on hydrocarbons.
The hydroformylation of cyclododeca-1,5,9-triene is known (U.S. Pat. Nos. 3,312,742 and 3,354,229; French Pat. No. 1,411,448 or British Pat. No. 1,161,147). According to these patents, corresponding C.sub.13 -alcohols and mixtures containing formyl cyclodocane in addition to formyl cyclodecene, formyl cyclodocadiene and the C.sub.13 -alcohol can be produced from cyclododecatriene using cobalt catalysts. Even under controlled conditions, the yield of formyl cyclododecane does not exceed 40% of the theoretical. Hydroxymethyl cyclododecanes are always obtained as the main product. Even under conditions under which formyl cyclooctane is obtained in a 56.7% yield from cycloocta-1,5-diene, hydroxymethyl cyclododecane is almost exclusively formed from cyclododeca-1,5,9-triene.
The production of di- and tri-formyl cyclododecanes would appear to involve even greater difficulties.
The use of cobalt complexes with trialkyl phosphite ligands in the hydroformylation of cyclododecatriene also results primarily in the formation of hydroxymethyl cyclododecane.